Photoinduced Metal- and Photosensitizer-Free Decarbonylative C–H Alkylation of Cyclic Sulfamidate Imines

Fang, Ling; Yu, Jiawen; Yu, Zhiyun; Tong, Feifei; Zhang, Chun; Hu, Dandan; Zhang, Jun-Qi; Ren, Hongjun

doi:10.1021/acs.joc.3c02088

Cited by 11 publications

(3 citation statements)

References 45 publications

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“…The acylated benzo[ d ]thiazoles are prone to cathodic reduction, resulting in the formation of hydroxyalkylated products. Additionally, decarbonylative alkylation product 30 was obtained in 26% yield by the reaction of 1 and pivalaldehyde due to the strong stability of the tert -butyl radical . A plausible mechanism for the formation of 27 – 29 and 30 has been provided in the Supporting Information (Figures S5 and S6).…”

Section: Resultsmentioning

confidence: 99%

Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process

He,

Pan,

Hou

et al. 2024

J. Org. Chem.

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An organocatalyzed photoelectrochemical method for the generation of acyl and phosphoryl radicals from formamides, aldehydes, and phosphine oxides has been developed. This protocol utilizes 9,10-phenanthrenequinone (PQ) as both a molecular catalyst and a hydrogen atom-transfer (HAT) reagent, eliminating the requirement for external metal-based reagents, HAT reagents, and oxidants. The generated acyl radicals can be applied to a range of radical-mediated transformation reactions, including C–H carbamoylation of heteroarenes, intermolecular tandem radical cyclization of CF3-substituted N-arylacrylamides, as well as intramolecular cyclization reactions. The use of acyl radicals in these transformations offers an efficient and sustainable approach to accessing structurally diverse carbonyl compounds.

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Section: Resultsmentioning

confidence: 99%

Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process

He,

Pan,

Hou

et al. 2024

J. Org. Chem.

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“…Hence, it would be helpful to explore a simple yet efficient strategy for the construction of these compounds using diazoalkanes as radical acceptors. On the basis of our interest in the synthesis of N -heterocycles, we examined the reaction of ethyl diazoacetate ( 1a ), iodopentafluoroethane ( 2a ) and 1-aminopyridinium ylide ( 3a ) as a model substrate. During these trials, we found that diazoalkanes could act as radical acceptors in conjunction with visible light to allow the construction of pyrazolo[1,5- a ]pyridine with a CF 3 group ( 4a ) in 70% yield (Table , entry 1).…”

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confidence: 99%

Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds

Zhao,

Liu,

Zhang

et al. 2024

Org. Lett.

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This work demonstrates the synthesis of a variety of perfluoroalkyl heterocycles via a visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/S N V-type/cyclization sequences follow the radical addition reaction of a diazoester, which differs from the current role of diazoesters as radical precursors/acceptors. This transformation demonstrates excellent functional group compatibility and allows for the modification of many bioactive molecules with diazoesters. Such a reaction could represent a novel approach to the photochemical transformation of diazo compounds.

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“…2 The Minisci-type reaction involving a radical process has long been recognized as a straightforward and effective approach for C(sp 2 )–H functionalization. 3 Extensive research has been conducted on the C(sp 2 )–H alkylation of heteroarenes using various alkyl radical precursors such as carboxylic acids, 4 oxalates, 5 alkyl borides, 6 alkyl halides, 7 aldehydes, 8 alcohols, 9 and NHPI esters 10 etc. In addition to these methods, the dehydrogenation cross-coupling of heteroarenes with C(sp 3 )–H compounds offers an appealing alternative for achieving C(sp 2 )–H alkylation of heteroarenes.…”

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confidence: 99%

Organophotoelectrocatalytic C(sp²)–H alkylation of heteroarenes with unactivated C(sp³)–H compounds

Wan,

Wu,

Hou

et al. 2024

Chem. Commun.

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Photoinduced Metal- and Photosensitizer-Free Decarbonylative C–H Alkylation of Cyclic Sulfamidate Imines

Cited by 11 publications

References 45 publications

Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process

Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process

Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds

Organophotoelectrocatalytic C(sp²)–H alkylation of heteroarenes with unactivated C(sp³)–H compounds

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Photoinduced Metal- and Photosensitizer-Free Decarbonylative C–H Alkylation of Cyclic Sulfamidate Imines

Cited by 11 publications

References 45 publications

Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process

Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process

Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds

Organophotoelectrocatalytic C(sp2)–H alkylation of heteroarenes with unactivated C(sp3)–H compounds

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Organophotoelectrocatalytic C(sp²)–H alkylation of heteroarenes with unactivated C(sp³)–H compounds